Amino derivatives of dibenzofuran



Patented Aug. 11, 1953 AMINO DERIVATIVES or DIBENZOFURAN Wilhelm Wenner,Upper Montclair, N. J., assignor to Hoflmann-La Roche Inc., Nutley, N. Ja corporation of New Jersey No Drawing.

Original application October 28, 1949, Serial No. 124,260.

Divided and this application November 23, 1951, Serial No. 257,965

7 Claims. (01. 260-3462) The present invention relates to2-benzylaminomethyl-dibenzofuran and2-cyclohexylaminomethyl-dibenzofuran and to the acid addition saltsthereof. These compounds are of interest for chemo-therapeutic purposes,and, more particularly, they are useful in combatting fungus infections.

In general, the bases of the invention can be repared by reacting2-chloromethyl-dibenzofuran with benzylamine or cyclohexylamine. Thereagents can be employed in equimolecular amounts, but it isadvantageous to employ at least two mols of the nitrogen base to one molof 2- chloromethyl-dibenzofuran, the second mol of the nitrogen baseserving to bind or neutralize the hydrochloric acid formed in thereaction. The reaction is preferably carried out in the presence of anorganic solvent, as for example, ether, ethyl alcohol, benzene, toluene,dioxane, and the like.

The bases of the invention are readily soluble in the common organicsolvents, but are practically insoluble in water. They readily formsalts with inorganic and. organic acids, for example, with hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid,benzoic acid, tartaric acid, oxalic acid, citric acid, salicylic acid,and the like.

The following examples will serve to illustrate the invention.

Example 1 Ten grams of 2-ch1oromethyl-dibenzofuran and 12 grams ofbenzylamine were dissolved in 100 cc. of absolute alcohol. The mixturewas warmed to '70-80 C. for five hours. The solution was diluted with500 cc. of ether and 500 cc. of water. The ether layer was separated andextracted with 3 per cent hydrochloric acid. Crystals separated within ashort time from the acid extract. The crystals were filtered, and uponrecrystallization from water or from alcohol-ether, 2-benzylaminomethyldibenzofuran hydrochloride, M. P. 234 0., was obtained.

Example 2 Ten grams of 2-chloromethyl-dibenzofuran were dissolved in cc.of toluene. Eleven grams of cyclohexylamine were added. The mixture waswarmed on a steam bath for three hours. It was then filtered from thecyclohexylamine hydrochloride which formed. The filtrate was washed withwater and was then extracted with 3 per cent hydrochloric acid. An oilseparated from the acid extract and soon crystallized. The crystals werepurified by recrystallization from water. The2-cyclohexylaminomethyl-dibenzofuran hydrochloride thus obtained has anM. P. of 248 C. I

This application is a division of my copending application Serial No.124,260, filed October 28, 1949, now abandoned.

I claim:

1. A compound selected from the group consisting of2-benzylaminomethy1-dibenzofuran and its addition salts and2-cyclohexylaminomethyl-dibenzofuran and its acid addition salts.

2. 2-benzylaminomethy1-dibenzofuran.

3. An acid addition salt of the compound of claim 2.

4. A hydrochloride of the compound of claim 2.

5. 2-cyclohexylaminomethyl-dibenzofuran.

6. An acid addition salt of the compound of claim 5.

7. A hydrochloride of the compound of claim 5.

WILHELM WENNER.

References Cited in the file of this patent Willis, CA (1944), page 739.

Kilpatrick, CA vol. 31 (1937), page 1800.

Gilman, J. Am. Chem. Soc, pp. 2836-2849, vol. 61 (1939).

1. A COMPOUND SELECTED FROM GROUP CONSISTING OF 2-BENZYLAMINOMETHYL -DIBENZOFURAN AND ITS ADDITION SALTS AND2-CYCLOHEXYLAMINOMETHYL-DIBENZOFURAN AND ITS ACID ADDITION SALTS.